Ketomethylenebestatin: Synthesis and Aminopeptidase Inhibition
| Autor: | Cirilo Pérez, Ma Teresa García-López, Isabel Gomez-Monterrey, Julia Castro-Pichel, Rosario Herranz, S. Vinuesa |
|---|---|
| Rok vydání: | 1993 |
| Předmět: |
chemistry.chemical_classification
Ketone biology Swine Stereochemistry Decarboxylation Diastereomer Pharmaceutical Science In Vitro Techniques Alkylation Aminopeptidases Aminopeptidase chemistry.chemical_compound chemistry Heptanoic Acids Leucine Enzyme inhibitor Bromide Drug Discovery biology.protein Animals Aliphatic compound |
| Zdroj: | Archiv der Pharmazie. 326:395-398 |
| ISSN: | 1521-4184 0365-6233 |
| DOI: | 10.1002/ardp.19933260705 |
| Popis: | The synthesis of (6R,5S,2RS)-6-amino-5-hydroxy-2-isobutyl-4-oxo-7- phenylheptanoic acid (9), a carbaanalogue of the aminopeptidase (AP) inhibitor bestatin (1) is described. This synthesis was carried out by a malonic ester alkylation with the suitably protected halomethyl ketone of (2S,3R)-AHPBA*), followed by a second alkylation with isobutyl bromide of the resulting 4-ketodiester, and subsequent decarboxylation and deprotection. The inhibitory potencies of the 1:1 diastereomeric mixture 9 against AP-B, AP-M and Leu-AP were approximately 10-fold lower than those of bestatin. |
| Databáze: | OpenAIRE |
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